US1860751A - New triarylmethane dyestuffs - Google Patents

New triarylmethane dyestuffs Download PDF

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Publication number
US1860751A
US1860751A US354981A US35498129A US1860751A US 1860751 A US1860751 A US 1860751A US 354981 A US354981 A US 354981A US 35498129 A US35498129 A US 35498129A US 1860751 A US1860751 A US 1860751A
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US
United States
Prior art keywords
new
magenta
parts
triarylmethane
blue
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US354981A
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English (en)
Inventor
Rodd Ernest Harry
Sharp Frederick Lawrence
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Publication date
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents

Definitions

  • magenta bodies such as pararosaniline, rosaniline and their homologues by heating with aniline, toluidines, or naphthylamines in presence of a catalyst, has long been practised, and sulphonation of the products gives the well-known alkali blues and soluble blues.
  • homologues of rosaniline prepared from mixtures of aniline and o-toluidine it is well known that the greater the proportion of o-toluidine which enters into reaction, thereby increasing the yield, the less readily can the'resulting rosaniline be phenylated, (of. Lambrecht, Berichte, 1907, 40, 249).
  • Example 1.1O parts of pararosaniline are mixed with parts of p-phenetidine and 2 parts of benzoic acid and the whole gradually heated to 160 C. This temperature is main-l tained for two hours, or for such a period as is required to obtain a desired shade.
  • the melt is then added to 400 parts of 5% hydrochloric acid; the spirit blue separates andis removed by filtration, washed and dried. From the filtrate the excess of p-phenetidine is recovered.
  • the exact constitution of the dye is not definitely known, but it is thought to be a mixture of mono-, di-, and triarylated idue O-ooun a 10 parts of the spirit blue are added to 40 parts of concentrated sulphuric acid at such a rate as to prevent the temperature rising wherein R represents hydrogen or the resabove 25 C. When the addition is complete the temperature is gradually raised to 70 C.
  • the sulphonation mixture is addedto a solution of common salt which precipitates the sulphonic acid.
  • the sulphonic acid is filtered oif and converted to its sodium salt. by dissolving in caustic soda solution.
  • the resulting neutral solution is evaporated to dryness to obtain the dyestuii, which dyes wool a bright greenish-blue shade.
  • the constitution of the dye is not definitely known but it is thoughtv to be a mixture of mono-, diand triar lated new magenta which in the form of the carbinols may be represented by the probable formula HaC CH3 TQ H H H RHeQ OH H3 ⁇ yearn
  • the sulphonation is carried out by adding 10 parts of the spirit blue to 4.0 parts of concentrated sulphuric acid at a temperature below 25 C.
  • a process for the production of new dyes of the triarylmethane series which consists in condensing a magenta body having in the form of the carbinol the probable for mula Ra lia HQN O-nm wherein R represents hydrogen or a methyl group, with an alkoxyaminobenzene and sulphonating the resultant product.
  • step 1 the production of new dyes of the triarylmethane series which consists in condensing a magenta body having in the form of the carbinol the probable formula HQNHQ on V Ra i V wherein R represents hydrogen or a methyl wherein It represents hydrogen or'a methyl group, with an alkoxyaminobenzene and sul-- phonating the resultantproduct, and which, in the form of its sodium salt, are soluble in water and dye wool blue shades.
  • the dye of the'triarylmethane-series which can be obtained by condensing pararosaniline with paraphenetidine and sulphonating the resulting product, and which, in the form of its sodium salt, is soluble in water and dyes wool blue shades.
  • a process for the production of new dyes of the triarylmethane series which comprises condensing a magenta body having in the form of the carbinol the probable formula a l a HzN ONHZ /C HzN- OH wherein R represents hydrogen or a methyl group, with an alkoxy amino benzene having the probable formula wherein R represents an alkyl group and sulphonating the resulting mixture.
  • the dyes of the triarylmethane series which can be obtained by condensing a magenta body having in the form of the carbinol the probable formula r R3 H 011 wherein R represents hydrogen or a methyl group, with an alkoxy amino benzene having the probable formula HzN-OO-Rz probable formula group, with an alkoxy amino benzene having the probable formula wherein R represents an alkyl group, and which are soluble in spirit with a blue solu- ,tion.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Coloring (AREA)
  • Cosmetics (AREA)
  • Color Printing (AREA)
US354981A 1928-04-18 1929-04-13 New triarylmethane dyestuffs Expired - Lifetime US1860751A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB11461/28A GB308906A (en) 1928-04-18 1928-04-18 New triarylmethane dyestuffs

Publications (1)

Publication Number Publication Date
US1860751A true US1860751A (en) 1932-05-31

Family

ID=9986663

Family Applications (1)

Application Number Title Priority Date Filing Date
US354981A Expired - Lifetime US1860751A (en) 1928-04-18 1929-04-13 New triarylmethane dyestuffs

Country Status (4)

Country Link
US (1) US1860751A (de)
DE (1) DE508499C (de)
FR (1) FR672921A (de)
GB (1) GB308906A (de)

Also Published As

Publication number Publication date
GB308906A (en) 1929-04-04
DE508499C (de) 1930-09-27
FR672921A (fr) 1930-01-08

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